Везде

RAS Chemistry & Material ScienceЖурнал общей химии Russian Journal of General Chemistry

  • ISSN (Print) 0044-460X
  • ISSN (Online) 3034-5596

Dyes for Photoelectronics Based on (12H-Quinoxalino[2,3-b]phenoxazinyl)phenyl Derivatives

You can
PII
S3034559625090056-1
DOI
10.7868/S3034559625090056
Publication type
Article
Status
Published
Authors
E. P. Ivakhnenko
  • Affiliation: Institute of Physical and Organic Chemistry, Southern Federal University
N. I. Omelichkin
  • Affiliation: Institute of Physical and Organic Chemistry, Southern Federal University
P. A. Knyazev
  • Affiliation: Institute of Physical and Organic Chemistry, Southern Federal University
S. E. Kislicin
  • Affiliation: Institute of Physical and Organic Chemistry, Southern Federal University
A. V. Chernyshev
  • Affiliation: Institute of Physical and Organic Chemistry, Southern Federal University
A. E. Aleksandrov
  • Affiliation: A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
A. R. Tameev
  • Affiliation: A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
V. I. Minkin
  • Affiliation: Institute of Physical and Organic Chemistry, Southern Federal University
Volume/ Edition
Volume 95 / Issue number 9-10
Pages
395-405
Abstract
The acylation reactions of 4-(2,4-di-tert-butyl-10-methoxy-12H-quinoxalino[2,3-b]phenoxazin-12-yl)aniline with acid chlorides of various structures, including substituents with the properties of anchor groups (hydroxy-phenyl, carboxyl, acrylamide, methacrylamide), as well as isobenzofuran-1,3-dione and dihydrofuran-2,5-dione led to the formation of the corresponding 4-(2,4-di-tert-butyl-10-methoxy-12H-quinoxalino[2,3-b]phenoxazin-12-yl)anilides in high yield (79–92%). The resulting amides were characterized by strong (ε = 2.94–4.26 ∙ 10 M∙cm) absorption bands in the range of 470–630 nm with maxima at 548–551 nm. They also exhibit a photovoltaic effect and high open-circuit parameters (up to 0.57 V) in DSSC solar cells and the ability to exhibit photodiode properties.
Keywords
12H-хиноксалино[2,3-b]феноксазины андигирование амиды фотовольтанческий эффект DSSC фотодиодные свойства
Date of publication
21.12.2025
Year of publication
2025
Number of purchasers
0
Views
41

References

  1. 1. Nicolas Y., Allama F., Lepeltier M., Massin J., Castet F., Ducasse L., Hirsch L., Boubegtiten Z., Jonusauskas G., Olivier C., Toupance T. // Chem. Eur. J. 2014. Vol. 20. P. 3678. doi 10.1002/chem.201303775
  2. 2. Di C., Li J., Yu G., Xiao Y., Guo Y., Liu Y., Qian X., Zhu D. // Org. Lett. 2008. Vol. 10. P. 3025. doi 10.1021/ ol8008667
  3. 3. Allama F., Gherraf N., Nicolas Y., Toupance T., Khatmi D. // Acta Sci. Nat. 2019. Vol. 6. P. 42. doi 10.2478/ asn-2019-0006
  4. 4. Gong X., Han P., Wen H., Sun Y., Zhang X., Yang H., Lin B. // Eur. J. Org. Chem. 2017. Vol. 25. P. 3689. doi 10.1002/ejoc.201700393
  5. 5. Schaffroth M., Lindner B.D., Vasilenko V., Rominger F., Bunz U.H.F. // J. Org. Chem. 2013. Vol. 78. P. 3142. doi 10.1021/jo400092r
  6. 6. Shi X., Chi C. // Top. Curr. Chem. Collect. Cham: Springer International Publishing, 2018. P. 169. doi 10.1007/9783-319-93302-3_4
  7. 7. Bunz U.H.F., Freudenberg J. // Acc. Chem. Res. 2019. Vol. 52. P. 1575. doi 10.1021/acs.accounts.9b00160
  8. 8. Ivakhnenko E.P., Romanenko G.V., Makarova N.I., Kovalenko A.А., Knyazev P.A., Rostovtseva I.A., Starikov A.G., Minkin V.I. // Dyes Pigm. 2020. Vol. 176. P. 108174. doi 10.1016/j.dyepig.2019.108174
  9. 9. Ivakhnenko E.P., Knyazev P.A., Omelichkin N.I., Makarova N.I., Starikov A.G., Aleksandrov A.E., Ezhov A.V., Tameev A.R., Demidov O.P., Minkin V.I. // Dyes Pigm. 2022. Vol. 197. P. 109848. doi 10.1016/j.dyepig.2021.109848
  10. 10. Ivakhnenko E.P., Romanenko G.V., Kovalenko A.A., Revinskii Yu.V., Knyazev P.A., Kuzmin V.A., Minkin V.I. // Dyes Pigm. 2018. Vol. 150. P. 97. doi 10.1016/ j.dyepig.2017.11.009
  11. 11. Минкин В.И., Князев П.А., Омеличкин Н.И., Макарова Н.И., Бородкин Г.С., Стариков А.Г., Демидов О.П., Ивахненко Е.П. // Изв. АН. Сер. хим. 2023. Т. 72. С. 669; Minkin V.I., Knyazev P.A., Omelichkin N.I., Makarova N.I., Borodkin G.S., Starikov A.G., Demidov O.P., Ivak hnenko E.P. // Russ. Chem. Bull. 2023. Vol. 72. P. 669. doi 10.1007/s11172-023-3831-4
  12. 12. Shen J., Li Y., He J.-H. // Dyes Pigm. 2016. Vol. 127. P. 187. doi 10.1016/j.dyepig.2015.11.029
  13. 13. Cardona C.M., Li W., Kaifer A.E., Stockdale D., Bazan G.C. // Adv. Mater. 2011. Vol. 23. P. 2367. doi 10.1002/adma.201004554
  14. 14. Najm A.S., Alwash S.A., Sulaiman N.H., Chowdhury M.S., Techato K. // Environ. Prog. Sustain. Energy. 2023. Vol. 42. P. e13955. doi 10.1002/ep.13955
  15. 15. Juska G., Arlauskas K., Viliunas M., Kocka J. // Phys. Rev. Lett. 2000. Vol. 84. P. 4946. doi 10.1103/PhysRevLett.84.4946
  16. 16. Parker C.A., Rees W.T. // Analyst. 1960. Vol. 85. P. 587.
  17. 17. Magde D., Brannon J.H., Cremers T.L., Olmsted J. // J. Phys. Chem. 1979. Vol. 83. P. 696. doi 10.1021/ j100469a012
  18. 18. Zhang L., Yang X., Li S., Hagfeldt A., Sun L. // Solar RRL. 2020. Vol. 4. P. 1900436. doi 10.1002/solr.201900436
  19. 19. Ezhov A.V., Aleksandrov A.E., Zhdanova K.A., Zhdanov A.P., Klyukin I.N., Zhizhin K.Yu., Bragina N.A., Mironov A.F., Tameev A.R. // Synth. Met. 2020. Vol. 269. P. 116567. doi 10.1016/j. synthmet.2020.116567
  20. 20. Saranin D.S., Mazov V.N., Luchnikov L.O., Lypenko D.A., Gostishev P.A., Muratov D.S., Podgorny D.A., Migunov D.M., Didenko S.I., Orlova M.N., Kuznetsov D.V., Tameev A.R., Di Carlo A. // J. Mater. Chem. (C). 2018. Vol. 6. P. 6179. doi 10.1039/C8TC01169A
  21. 21. Stephen M., Genevičius K., Juška G., Arlauskas K., Hiorns R.C. // Polym. Int. 2007. Vol. 66. P. 13. doi 10.1002/pi.5274
QR
Translate

Индексирование

Scopus

Scopus

Scopus

Crossref

Scopus

Higher Attestation Commission

At the Ministry of Education and Science of the Russian Federation

Scopus

Scientific Electronic Library